Romantic Getaway Guide to St. Augustine, Florida

1. Trolley tour of the historic district: A Trolley Tour Pass is a recommended purchase, offering easy hop-on and hop-off experiences that allow you to explore the rich history of America's oldest city at your own pace.

2. The Old Jail: Built in 1891 and surprisingly in operation until the 1950s, this site delivers a mix of eerie charm and real insight into past life in St. Augustine. With preserved jail cells and original artifacts, you'll get a true sense of what incarceration was like a century ago. It's chilling and fascinating.

3. The Medieval Torture Museum: Equal parts terrifying and theatrical, this attraction is like stepping into a very twisted history lesson. Wax figures in disturbing poses, hands-on torture devices, and interactive exhibits will leave you thinking: "People really did this?!" You'll laugh, you'll squirm, and you might even take a selfie in a torture cage—because hey, what's romance without a little shared trauma?

4. Father Lopez and the Great Cross: Part of the trolley hop-on hop-off tour, this sight is a beacon of faith by the Diocese of St. Augustine in honor of the 400th anniversary of the city. At 208 feet tall, it marks the landing site of Pedro Menendez de Aviles and commemorates the city's first Catholic Mass.

5. St. George Street Pedestrian Mall: Wandering down St. George Street is like stepping back in time—cobblestone paths, centuries-old architecture, and a vibrant atmosphere filled with life and charm. We strolled past ice cream parlors, boutique shops, and cozy cafes, each offering a little piece of St. Augustine's soul. Expect uneven ground in some areas—it adds to the character, but wear comfortable shoes. Tip: Travel in the early evening when the lights twinkle, the musicians warm up, and the energy is just right.

1. The Reef: One of the only oceanfront venues with window views of the sand and waves, The Reef offers a diverse menu of seafood, beef, and poultry that's always fresh, under the direction of Chef Denzel Aponte. Look into upcoming full moon events, which are celebrated with special drinks and happy hour rates. This restaurant does require reservations—don't miss out on Sunday brunch with music or Sunday happy hour from 4:30 to 7 pm with food and drink discounts.

2. River & Fort Restaurant and Rooftop Lounge: Located right at the main intersection in the heart of historic St. Augustine with coastal breeze and stunning views, River & Fort Restaurant features locally inspired dishes, a refined but relaxed vibe, and an ambiance that perfectly captures the spirit of Florida. We were lucky to sit at the bar, where we met Austin, an incredible bartender who made the entire experience even better. His specialty cocktail, Blacksmith, was smoky, bold, and full of character.

3. Columbia Restaurant: This historic eatery on St. George Street has served award-winning Spanish-Cuban dishes in a beautifully tiled dining room, just steps from the water, since 1905. They don't require reservations but highly recommend you make them. They are open until 10 pm and they do have a dress code: no baseball caps, and men must wear sleeves indoors.

4. Bin 39 Wine Bar: A hidden gem of romance nestled in a charming courtyard setting with live music and light bites. Visiting this spot was like walking into a romantic European dream, with cute patio chair dining and flowers on the tables. Each glass of wine felt thoughtfully curated, and the setting made it easy to lose track of time. Whether you're on your first date or celebrating a lifetime together, there's something magical about sipping wine under the stars in this little hidden corner of St. George Street.

5. Collage: Voted one of OpenTable's Top 100 Romantic Restaurants in 2024, Collage is renowned for its intimate atmosphere and globally inspired cuisine. Walking in, the huge wooden doors framed with beautiful flowering plants set a warm and inviting vibe. Their seasonal menu features innovative dishes crafted fresh with local ingredients. The candlelit dining room, adorned with local artwork and rustic touches, creates a cozy and romantic setting. We had lobster ravioli and I've been craving it ever since. Silky pasta, rich flavor, and the kind of dish you remember long after the night ends.